WO1999026942A1 - 5-(2-imidazolinylamino)-benzimidazole, derives et procedes de preparation et d'utilisation de ces derniers en tant qu'agonistes du recepteur alpha-adrenergique ayant une meilleure stabilite metabolique - Google Patents
5-(2-imidazolinylamino)-benzimidazole, derives et procedes de preparation et d'utilisation de ces derniers en tant qu'agonistes du recepteur alpha-adrenergique ayant une meilleure stabilite metabolique Download PDFInfo
- Publication number
- WO1999026942A1 WO1999026942A1 PCT/US1998/024694 US9824694W WO9926942A1 WO 1999026942 A1 WO1999026942 A1 WO 1999026942A1 US 9824694 W US9824694 W US 9824694W WO 9926942 A1 WO9926942 A1 WO 9926942A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- hydrogen
- group
- cyano
- halo
- Prior art date
Links
- 0 C[n](cnc1c2*)c1c(*)cc2N Chemical compound C[n](cnc1c2*)c1c(*)cc2N 0.000 description 1
- JOYPSAMLHRAXHQ-UHFFFAOYSA-N Cc(c(N=C1NCCN1)c1C)cc2c1nc[nH]2 Chemical compound Cc(c(N=C1NCCN1)c1C)cc2c1nc[nH]2 JOYPSAMLHRAXHQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- R2, R3, R4 or R5 is other than hydrogen or fluorine;
- R1 is methyl and both R2 and R5 are hydrogen, R3 is other than methyl or halo;
- R3 is cyano, R1 is methyl;
- R5 is hydrogen, methyl, amino, methoxy, hydroxy, cyano or halo.
- Preferred R5 is hydrogen, methyl, or halo.
- at least one of R2, R3, R4, and R5 is other than hydrogen or fluorine.
- R1 is methyl and both R2 and R5 are hydrogen, then R3 is other than methyl or halo.
- R3 is cyano, R1 is methyl.
- acids-addition salts include, but at not limited to hydrochloride, hydrobromide, hydroiodide, sulfate, hydrogensulfate, acetate, trifluoroacetate, nitrate, maleate, citrate, fumarate, formate, stearate, succinate, mallate, malonate, adipate, glutarate, lactate, propionate, butyrate, tartrate, methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate, dodecyl sulfate, cyclohexanesulfamate, and the like.
- the compounds of the present invention are useful in treating many medical disorders, including for example, respiratory disorders, ocular disorders, gastrointestinal disorders, disorders associated with sympathetic nervous system activity, migraine, peripheral pain, and disorders where vasoconstriction would provide a benefit.
- One tablet is swallowed by a patient with nasal congestion.
- the congestion is substantially diminished.
- One tablet is placed under the tongue of a patient with nasal congestion and allowed to dissolve. The congestion is rapidly and substantially diminished.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9815017-0A BR9815017A (pt) | 1997-11-24 | 1998-11-20 | Derivados de 5-(2-imidazolinilamino)-benzimidazol, sua preparação e seu uso como agonistas de alfa-adrenorreceptores com estabilidade metabólica aperfeiçoada |
HU0101469A HUP0101469A3 (en) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as alpha-adrenoceptor agonists with improved metabolic stability |
NZ504707A NZ504707A (en) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability |
EP98959512A EP1037887B1 (fr) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole, derives et procedes de preparation et d'utilisation de ces derniers en tant qu'agonistes du recepteur alpha-adrenergique ayant une meilleure stabilite metabolique |
DE69825075T DE69825075T2 (de) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazol derivate, deren herstellung und deren verwendung als .alpha.-adrenoceptor agonisten mit verbesserter metabolischer stabilität |
JP2000522100A JP2001524478A (ja) | 1997-11-24 | 1998-11-20 | 5−(2−イミダゾリニルアミノ)−ベンゾイミダゾール誘導体類、それらの調製および改良された代謝安定性を有するアルファアドレナリン受容体作動薬としてのそれらの使用 |
SK779-2000A SK7792000A3 (en) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as alpha-adrenoceptor agonists with improved metabolic stability |
AT98959512T ATE271048T1 (de) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazol derivate, deren herstellung und deren verwendung als .alpha.-adrenoceptor agonisten mit verbesserter metabolischer stabilität |
AU15299/99A AU741774B2 (en) | 1997-04-15 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability |
IL13630398A IL136303A (en) | 1997-11-24 | 1998-11-20 | History -5 (-2 Imidazolinylamino) - Banimidazole, preparation and use as an α-adororeceptor agonists |
US09/554,698 US6486190B1 (en) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability |
KR1020007005675A KR20010032435A (ko) | 1997-11-24 | 1998-11-20 | 5-(2-이미다졸리닐아미노)벤즈이미다졸 유도체, 그의 제조및 대사 안정성이 개선된 알파-아드레날린수용체아고니스트로서의 그의 용도 |
CA002311344A CA2311344C (fr) | 1997-11-24 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole, derives et procedes de preparation et d'utilisation de ces derniers en tant qu'agonistes du recepteur alpha-adrenergique ayant une meilleurestabilite metabolique |
NO20002655A NO20002655L (no) | 1997-11-24 | 2000-05-24 | 5-(2-imidazolinylamino) -benzimidazol derivater, fremstilling og anvendelse derav som <alfa>-adrenoceptoragonister med forbedret metabolisk stabilitet |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6676797P | 1997-11-24 | 1997-11-24 | |
US60/066,767 | 1997-11-24 | ||
US6670097P | 1997-11-25 | 1997-11-25 | |
US60/066,700 | 1997-11-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1999026942A1 true WO1999026942A1 (fr) | 1999-06-03 |
WO1999026942A8 WO1999026942A8 (fr) | 2000-08-03 |
Family
ID=26747058
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/024694 WO1999026942A1 (fr) | 1997-04-15 | 1998-11-20 | 5-(2-imidazolinylamino)-benzimidazole, derives et procedes de preparation et d'utilisation de ces derniers en tant qu'agonistes du recepteur alpha-adrenergique ayant une meilleure stabilite metabolique |
Country Status (23)
Country | Link |
---|---|
US (1) | US6486190B1 (fr) |
EP (1) | EP1037887B1 (fr) |
JP (1) | JP2001524478A (fr) |
KR (1) | KR20010032435A (fr) |
CN (1) | CN1284073A (fr) |
AT (1) | ATE271048T1 (fr) |
BR (1) | BR9815017A (fr) |
CA (1) | CA2311344C (fr) |
CO (1) | CO4970802A1 (fr) |
DE (1) | DE69825075T2 (fr) |
ES (1) | ES2223143T3 (fr) |
HU (1) | HUP0101469A3 (fr) |
IL (1) | IL136303A (fr) |
IN (1) | IN190809B (fr) |
NO (1) | NO20002655L (fr) |
NZ (1) | NZ504707A (fr) |
PE (1) | PE133699A1 (fr) |
PL (1) | PL340711A1 (fr) |
RU (1) | RU2193562C2 (fr) |
SK (1) | SK7792000A3 (fr) |
TR (1) | TR200002242T2 (fr) |
TW (1) | TW505642B (fr) |
WO (1) | WO1999026942A1 (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004074279A1 (fr) * | 2003-02-20 | 2004-09-02 | The Board Of Regents Of The University Of Nebraska | Procedes de fabrication de 6-[(4,5-dihydro-1h-imidazol-2-yl)amino-]-7-methyl-1h-benzimidazole-4-carbonitrile et forme preferee d'un sel de celui-ci |
WO2004074234A1 (fr) * | 2003-02-20 | 2004-09-02 | Lonza Ag | Procede de preparation de formamides n-substitutes |
US20050020600A1 (en) * | 2003-07-23 | 2005-01-27 | Scherer Warren J. | Methods of treating cutaneous flushing using selective alpha-2-adrenergic receptor agonists |
US7456183B2 (en) | 2001-04-09 | 2008-11-25 | Novartis Vaccines And Diagnostics, Inc. | Guanidino compounds |
US8420688B2 (en) | 2004-01-22 | 2013-04-16 | Allergan, Inc. | Method and therapeutic/cosmetic topical compositions for the treatment of rosacea and skin erythema using α1-adrenoceptor agonists |
WO2015073736A1 (fr) * | 2013-11-13 | 2015-05-21 | Arbor Pharmaceuticals, Llc | Méthodes et compositions de traitement du tdah |
EP2481412B1 (fr) * | 2004-05-25 | 2017-09-27 | Galderma Pharma S.A. | Composés, formulations et procédés pour traiter ou prévenir les troubles inflammatoires de la peau |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2842422B1 (fr) * | 2002-07-16 | 2006-06-30 | Univ Aix Marseille Ii | Compositions destinees au traitement des neuropathies peripheriques, preparation et utilisations |
TWI435729B (zh) | 2005-11-09 | 2014-05-01 | Combinatorx Inc | 治療病症之方法,組合物及套組 |
JP2015517980A (ja) * | 2012-02-27 | 2015-06-25 | アイ・セラピーズ・エル・エル・シー | 片頭痛の治療のための組成物および方法 |
MX2018006575A (es) * | 2015-11-30 | 2018-12-06 | Novus Therapeutics Inc | Composiciones y metodos para profilaxis otologica y tratamiento. |
EA030197B1 (ru) * | 2016-03-22 | 2018-07-31 | Общество С Ограниченной Ответственностью "Рубикон" | Таблетированная форма противовирусного лекарственного средства |
JP7163014B2 (ja) * | 2016-10-31 | 2022-10-31 | エスエス製薬株式会社 | 感冒薬 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995016685A1 (fr) * | 1993-12-17 | 1995-06-22 | The Procter & Gamble Company | Derives de 5-(2-imidazolinylamino)benzimidazole, leur preparation et leur utilisation en tant qu'agonistes de l'adrenocepteur alpha-2 |
WO1996004270A1 (fr) * | 1994-08-04 | 1996-02-15 | Synaptic Pharmaceutical Corporation | Nouveaux derives de benzimidazole |
WO1998046595A1 (fr) * | 1997-04-15 | 1998-10-22 | The Procter & Gamble Company | Composes de 5-(2-imidazolinylamino)benzimidazole utiles en tant qu'agonistes de l'adrenorecepteur alpha-2 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795970A (fr) | 1972-02-29 | 1973-08-27 | Pfizer | Nouveaux derives de quinoleine, quinoxaline et quinazoline er composition pharmaceutiques les contenant |
US4029792A (en) | 1972-02-29 | 1977-06-14 | Pfizer Inc. | (2-Imidazolin-2-ylamino) substituted -quinoxalines and -quinazolines as antihypertensive agents |
US4036976A (en) | 1973-04-05 | 1977-07-19 | Sandoz, Inc. | Substituted imidazolinylamino-indazoles |
US4217356A (en) | 1975-08-22 | 1980-08-12 | Sandoz Ltd. | 2-Imidazolinylamino-2,1,3-benzothiadiazoles |
US4398028A (en) | 1977-01-14 | 1983-08-09 | Sandoz Ltd. | Bicyclic heterocyclic amino derivatives |
EP0086428B1 (fr) | 1979-08-23 | 1987-07-29 | Beecham Group Plc | Composition vétérinaire anti-diarrhée, sa préparation et dispositif pour le dosage oral la contenant |
WO1982000824A1 (fr) | 1980-09-05 | 1982-03-18 | Geissmann F | Derives 1h et 2h de l'indazol et medicaments les renfermant |
FR2638356A1 (fr) | 1988-10-28 | 1990-05-04 | Anben | Nouveaux derives de la 2-arylimino-imidazolidine pour diminuer la pression intra-oculaire et traiter le glaucome |
US5281591A (en) | 1989-05-22 | 1994-01-25 | Allergan, Inc. | Combinations of selective alpha-adrenergic agonists and antagonists useful in lowering intraocular pressure |
US5180721A (en) | 1989-05-22 | 1993-01-19 | Allergan, Inc. | Combinations of selective alpha-adrenergic agonists and antagonists useful in lowering intraocular pressure |
US5231096A (en) | 1989-10-12 | 1993-07-27 | Allergan, Inc. | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
US5021416A (en) | 1989-10-31 | 1991-06-04 | Allergan, Inc. | Method for using (2-imidazolin-2-ylamino) quinoxalines to reduce or maintain intraocular pressure |
US5091528A (en) | 1990-09-12 | 1992-02-25 | Allergan, Inc. | 6- or 7- (2-imino-2-imidazolidine)-1,4-benzoxazines as α adrenergic agents |
-
1998
- 1998-11-20 EP EP98959512A patent/EP1037887B1/fr not_active Expired - Lifetime
- 1998-11-20 AT AT98959512T patent/ATE271048T1/de not_active IP Right Cessation
- 1998-11-20 ES ES98959512T patent/ES2223143T3/es not_active Expired - Lifetime
- 1998-11-20 HU HU0101469A patent/HUP0101469A3/hu unknown
- 1998-11-20 KR KR1020007005675A patent/KR20010032435A/ko active IP Right Grant
- 1998-11-20 JP JP2000522100A patent/JP2001524478A/ja not_active Withdrawn
- 1998-11-20 CN CN98813286A patent/CN1284073A/zh active Pending
- 1998-11-20 SK SK779-2000A patent/SK7792000A3/sk unknown
- 1998-11-20 CA CA002311344A patent/CA2311344C/fr not_active Expired - Fee Related
- 1998-11-20 US US09/554,698 patent/US6486190B1/en not_active Expired - Lifetime
- 1998-11-20 NZ NZ504707A patent/NZ504707A/xx unknown
- 1998-11-20 PL PL98340711A patent/PL340711A1/xx unknown
- 1998-11-20 WO PCT/US1998/024694 patent/WO1999026942A1/fr not_active Application Discontinuation
- 1998-11-20 DE DE69825075T patent/DE69825075T2/de not_active Expired - Lifetime
- 1998-11-20 BR BR9815017-0A patent/BR9815017A/pt not_active IP Right Cessation
- 1998-11-20 TR TR2000/02242T patent/TR200002242T2/xx unknown
- 1998-11-20 RU RU2000116269/04A patent/RU2193562C2/ru not_active IP Right Cessation
- 1998-11-20 IL IL13630398A patent/IL136303A/en not_active IP Right Cessation
- 1998-11-25 PE PE1998001146A patent/PE133699A1/es not_active Application Discontinuation
- 1998-11-25 CO CO98069637A patent/CO4970802A1/es unknown
- 1998-11-26 IN IN3539DE1998 patent/IN190809B/en unknown
-
1999
- 1999-02-10 TW TW087119586A patent/TW505642B/zh active
-
2000
- 2000-05-24 NO NO20002655A patent/NO20002655L/no not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995016685A1 (fr) * | 1993-12-17 | 1995-06-22 | The Procter & Gamble Company | Derives de 5-(2-imidazolinylamino)benzimidazole, leur preparation et leur utilisation en tant qu'agonistes de l'adrenocepteur alpha-2 |
WO1996004270A1 (fr) * | 1994-08-04 | 1996-02-15 | Synaptic Pharmaceutical Corporation | Nouveaux derives de benzimidazole |
WO1998046595A1 (fr) * | 1997-04-15 | 1998-10-22 | The Procter & Gamble Company | Composes de 5-(2-imidazolinylamino)benzimidazole utiles en tant qu'agonistes de l'adrenorecepteur alpha-2 |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7456183B2 (en) | 2001-04-09 | 2008-11-25 | Novartis Vaccines And Diagnostics, Inc. | Guanidino compounds |
WO2004074279A1 (fr) * | 2003-02-20 | 2004-09-02 | The Board Of Regents Of The University Of Nebraska | Procedes de fabrication de 6-[(4,5-dihydro-1h-imidazol-2-yl)amino-]-7-methyl-1h-benzimidazole-4-carbonitrile et forme preferee d'un sel de celui-ci |
WO2004074234A1 (fr) * | 2003-02-20 | 2004-09-02 | Lonza Ag | Procede de preparation de formamides n-substitutes |
US7304084B2 (en) | 2003-02-20 | 2007-12-04 | The Board Of Regents Of The University Of Nebraska | 6-[(4,5-Dihydro-1H-imidazol-2-yl)amino]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt |
EP1953146A1 (fr) | 2003-02-20 | 2008-08-06 | The Board of Regents of the University of Nebraska | Procédé de fabrication de 6-[(4,5-Dihydro-1H-Imidazol-2-yl) Amino-]-7-Methyl-1H-Benzimidazole-4-Carbonitrile et sa formule de sel préférée |
US20050020600A1 (en) * | 2003-07-23 | 2005-01-27 | Scherer Warren J. | Methods of treating cutaneous flushing using selective alpha-2-adrenergic receptor agonists |
US8420688B2 (en) | 2004-01-22 | 2013-04-16 | Allergan, Inc. | Method and therapeutic/cosmetic topical compositions for the treatment of rosacea and skin erythema using α1-adrenoceptor agonists |
US8815929B2 (en) | 2004-01-22 | 2014-08-26 | Allergan, Inc. | Method and therapeutic/cosmetic topical compositions for the treatment of rosacea and skin erythema using α1-adrenoceptor agonists |
US8877793B2 (en) | 2004-01-22 | 2014-11-04 | Allergan, Inc. | Method and therapeutic/cosmetic topical compositions for the treatment of rosacea and skin erythema using α1-adrenoceptor agonists |
EP2481412B1 (fr) * | 2004-05-25 | 2017-09-27 | Galderma Pharma S.A. | Composés, formulations et procédés pour traiter ou prévenir les troubles inflammatoires de la peau |
WO2015073736A1 (fr) * | 2013-11-13 | 2015-05-21 | Arbor Pharmaceuticals, Llc | Méthodes et compositions de traitement du tdah |
Also Published As
Publication number | Publication date |
---|---|
WO1999026942A8 (fr) | 2000-08-03 |
DE69825075T2 (de) | 2005-08-25 |
IN190809B (fr) | 2003-08-23 |
TR200002242T2 (tr) | 2000-11-21 |
BR9815017A (pt) | 2001-09-11 |
RU2193562C2 (ru) | 2002-11-27 |
CA2311344A1 (fr) | 1999-06-03 |
HUP0101469A2 (hu) | 2001-10-28 |
TW505642B (en) | 2002-10-11 |
IL136303A0 (en) | 2001-05-20 |
HUP0101469A3 (en) | 2003-01-28 |
US6486190B1 (en) | 2002-11-26 |
SK7792000A3 (en) | 2001-01-18 |
CO4970802A1 (es) | 2000-11-07 |
JP2001524478A (ja) | 2001-12-04 |
EP1037887B1 (fr) | 2004-07-14 |
ATE271048T1 (de) | 2004-07-15 |
CN1284073A (zh) | 2001-02-14 |
KR20010032435A (ko) | 2001-04-25 |
EP1037887A1 (fr) | 2000-09-27 |
NO20002655L (no) | 2000-07-24 |
PL340711A1 (en) | 2001-02-26 |
DE69825075D1 (de) | 2004-08-19 |
NO20002655D0 (no) | 2000-05-24 |
PE133699A1 (es) | 2000-03-05 |
IL136303A (en) | 2004-02-08 |
CA2311344C (fr) | 2006-02-07 |
NZ504707A (en) | 2002-11-26 |
ES2223143T3 (es) | 2005-02-16 |
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